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There aren’t many things I regret. But if I were hard-pressed, I’d have to say it’s a crying shame I never invested in Michael Kors: I met the superstar designer in the mid-’80s, when he was a fledgling designer, and I knew from the get-go he was destined for greatness. He had a focus, a clarity of vision and an uncanny understanding of how women wanted to dress. When Kors went on to become a household brand and his company went public in late 2011, shares went through the roof. It was a record-breaking IPO that set a new industry standard, and now Forbes is predicting that Kors himself will soon become fashion’s next billionaire.

Kors captured the world’s imagination with the notion of affordable luxury, and today, according to Digital Luxury Group, a market-intelligence organization, his label is the online world’s most sought-after U.S. brand.

But he is so much more than a mere fashion success: He’s a great guy and a compassionate philanthropist to boot, recently launching a campaign with Halle Berry called Watch Hunger Stop, which will help raise money through the sale of a version of Kors’ bestselling Runway watch. For each 100 Series watch sold, 100 meals will be provided to children through the UN’s World Food Program.

I recently caught up with Michael Kors at Holt Renfrew on Bloor St. W., where we talked about glamour, influence and age-appropriate dressing.

Q: A lot of women are obsessing over age-appropriate dressing. The lines are blurring and there’s so much that’s cross-generational, like your label. You’ve always told me you’ve got to dress for your spirit and your body, that it’s not about being age appropriate.

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A: I think the simple truth is you could be 16 years old and if you hate your knees, don’t wear a short skirt, even if every runway in the world is showing micro-mini dresses and shorts. And if you’re 70 and you have an incredible pair of legs, show them! I design for women and girls who know themselves. She has a good confidence level. She’s interested in fashion. She wants to know what’s going on. But first and foremost she knows her own self. On the other hand, I have to say I miss seeing people with grey hair. I think grey hair is great. In our craving for youth, we’ve walked away from the idea that you can be fabulous at every age

Q: You’ve obviously helped liberate us with that kind of philosophy, and also the whole idea of accessible glamour. When did glamour become a driving force with you?

A: When I was a kid growing up, I had all these women who represented different style points of view. My mother was and still is all about simplicity: She’s casual, low key. My grandmother was over the top. And then my mom’s sister-in-law — my dad’s sister — was full hippie chick. I think I’ve got this convergence and I understand all of these different women now because of these different icons.

But when it comes to myself, I love being casual and comfortable. Glamour used to be something separate. You were either practical or you were glamorous. But when I think about myself, I mean I’m in a crocodile shoe with a pair of sweatpants. Or I’ll wear the most expensive sweater to sleep in at the beach. There is such a thing as everyday glamour. The old-fashioned idea of glamour was that it was on this kind of pedestal.

To me, glamour is a weird convergence of American practicality and European indulgence. I remember being blown away watching women in Paris not really give a fig if something was that practical. It’s like “Fine! I’m going to buy a white winter coat. I don’t care if someone splashes it, I’ll deal with it.” New Yorkers are so, “Oh, I can’t wear the white coat. It’ll get dirty.” I think throwaway luxury is a little bit more European and I think the pragmatic kind of practicality is more North American.

Q: What do you hate about fashion these days? About the system and about the way it’s put out there?

A: I think sameness is a style killer. I see a lot of young designers who don’t really have their own fingerprint, their own vocabulary. They’re just going with the zeitgeist of what’s going on. Each designer has to represent something. And it has to evolve.

Q: Time recently voted you one of the top 100 most influential people in the world. How does success feel on the inside?

A: When I put on a fashion show, it can be fabulous, but I really don’t know if the clothes work until I actually see what I’ve designed being worn on the street, and more importantly, that she holds on to it, that it doesn’t get worn just once. So success feels a bit like a validation that you made the right choices in life, you’ve made the right creative choices. When I first met you, my idea of “foreign” was coming here to Toronto. We did not believe that there would be Michael Kors Stores in Kuala Lumpur and Dubai and Sydney and Rio de Janeiro.

We went to Bette Midler’s play, I’ll Eat You Last, last week and I grew up just blown away by her talent, her energy; I know her well and have her as a friend. When we went backstage to say hello, there’s Sherry Lansing, the first woman to run a studio, someone I’ve known for 25 years. And there’s Meryl Streep backstage, and I can’t imagine anyone reinventing herself more than she has done. And then Candice Bergen, who to me is just humour, intelligence, beauty and style. I looked around this room of women and I’m thought, “I know all of you and I’ve dressed all of you and I know your daughters and I’ve dressed your daughters.” I see all the generations. It’s an incredible feeling. That’s what success feels like.

Jeanne Beker is a contributing editor to the Star and host of Fashion Television Channel. Email jeanne@ctv.ca , follow on Twitter @jeanne_beker and watch her on CTV, E! and FashionTelevisionChannel.

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